ZOZO, Japan’s dominant online retailer of apparel and related lifestyle products, with approximately $1B in sales and $7B in market capitalization, has taken on a journey to recreate the world of apparel to the next level. [1] It aims to do so in two steps: 1) enable mass customization of private-labeled apparel products, and 2) quantify all aspects of what makes styles “cool” to become the global leader in product design. Will ZOZO be able to drive the industry in offering customized yet stylish product for the mass? What capabilities will differentiate who will win in the long haul?